1,031: Unlocking Operational Scale in Health Insurance Through AI and Data | Scott Blackley, CFO, Oscar Health

When Scott Blackley was asked in kindergarten what he wanted to be when he grew up, his answer was surprisingly clear: “I want to be an auditor.” This early ambition was no coincidence; his father was a partner at KPMG, and young Blackley grew up around the firm’s offices, imagining himself one day sitting at a big desk, overseeing important work. True to his dream, he eventually ended up following in his father’s footsteps to become a partner at KPMG and invest a dozen career years there.

Despite achieving his childhood goal and carrying on the family legacy, though, Blackley eventually found himself at a crossroads. “It was a tough decision to leave KPMG,” he recalls, “but some of the experiences that I had had involving other people’s business problems had made me want to own them.” This realization marked a turning point in his career that fueled his desire to take on more responsibility and solve problems on a firsthand basis.

This drive led Blackley to Oscar Health, where he stepped into the CFO role during a pivotal moment. Reflecting on his early days at the company, Blackley observes, “When I joined, one of the things that I walked in the door with was a commitment to myself that I was going to be thoughtful about taking the time to understand the situation and then decisive about making decisions.” Consequently, within 90 days, he would end up reorganizing the finance function to separate FP&A from the controller’s office and hiring a new leader to build a more structured finance organization—one capable of supporting Oscar Health’s ambitious plans for growth and transformation.